Formic Acid → HCID 67147726、化合物

HRID 506805ノート

反応式

HRID 506805 の反応式
[CH3:1][O:2][C:3]1N=[C:7]2[C:9]([C:13]3[N:24]([S:25]([C:28]4[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][CH:29]=4)(=[O:27])=[O:26])[C:16]4[N:17]=[CH:18][CH:19]=[C:20]([CH:21]=[N:22]O)[C:15]=4[CH:14]=3)=[CH:10][N:11]([CH3:12])[C:6]2=[CH:5][C:4]=1[O:35][CH3:36].[CH:37](O)=O>C(O)C.O.[Zn]>[O:2]([C:3]1[CH:37]=[C:7]2[C:6](=[CH:5][C:4]=1[O:35][CH3:36])[N:11]([CH3:12])[CH:10]=[C:9]2[C:13]1[N:24]([S:25]([C:28]2[CH:29]=[CH:30][C:31]([CH3:34])=[CH:32][CH:33]=2)(=[O:26])=[O:27])[C:16]2=[N:17][CH:18]=[CH:19][C:20]([CH2:21][NH2:22])=[C:15]2[CH:14]=1)[CH3:1]

参加物

6

反応物 2

HCID 284Formic AcidHCID 1363864872-(5,6-dimethoxy-1-methyl-1H-pyrrolo[3,2-b]pyridin-3-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-carbaldehyde oxime

生成物 1

HCID 67147726HCID 67147726、化合物

試薬・触媒・溶媒 3

HCID 23994Zinc触媒2 回HCID 702Ethanol溶媒HCID 962Water溶媒

実験手順

To a solution of 0.56 g of [2-(5,6-dimethoxy-1-methyl-1H-pyrrolo[3,2-b]pyridin-3-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-carbaldehyde oxime in 30 cm3 of ethanol and 25 cm3 of water, at a temperature in the region of 20° C., is added 0.216 g of zinc and 12 cm3 of concentrated formic acid. A further 0.216 g of zinc is added and the mixture is stirred for a further 24 hours. The reaction medium is stirred at this same temperature for 24 hours. The reaction medium is filtered through Celite and the filtrate is concentrated under reduced pressure. The residue obtained is purified by flash-pack chromatography (SiO2, dichloromethane/methanol 95/05, then dichloromethane/methanol/triethylamine 100/10/1, then dichloromethane/methanol/28% aqueous ammonia 100/10/2 by volume as eluents, Ar). The residue obtained is again purified by flash-pack chromatography (SiO2, dichloromethane/methanol/28% aqueous ammonia 460/40/1.5 by volume as eluents, Ar). 0.03 g of [2-(5,6-dimethoxy1-methyl-1H-indol-3-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]methylamine is obtained with the following characteristics:

後処理

  1. stirringThe reaction medium is stirred at this same temperature for 24 hours
  2. filtrationThe reaction medium is filtered through Celite
  3. concentrationthe filtrate is concentrated under reduced pressure
  4. customThe residue obtained
  5. customis purified by flash-pack chromatography (SiO2, dichloromethane/methanol 95/05
  6. customThe residue obtained
  7. customis again purified by flash-pack chromatography (SiO2, dichloromethane/methanol/28% aqueous ammonia 460/40/1.5 by volume as eluents, Ar)

出典と根拠

ORDレコード
ord-4148336754c242ebac22504df2382a54
出典データセット
uspto-grants-2010_08
特許番号
US07786114B2

反応ノート

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